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Inge Johnsson—Alamy

When it comes to choosing a retirement destination, the big challenge is whittling down the possibilities. One critical factor to consider: how much of a bite local taxes will take out of your nest egg. This year we went in search of the tax-friendliest small cities in the country—places big enough to have the amenities that retirees prize, such as access to great health care and recreation, but still affordable and compact enough to be manageable. Starting with states that have the lowest overall tax burdens, we zeroed in on locales that offer breaks on income, Social Security, pension, estate, and other taxes. These 12—a winner and runner-up in each region of the country—rose to the top.